


All I Want for Christmas is Drowley 2017

by songofhell



Category: Supernatural
Genre: Christmas, M/M
Language: English
Status: Completed
Published: 2017-12-18
Updated: 2017-12-24
Packaged: 2019-02-16 18:34:59
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 7,812
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13059759
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: All my works for my Drowley Christmas love week 2017.





	1. Give Me Your Best Shot

**Summary for the Chapter:**

> Day 1: Snow

Dean pulled his coat tighter around himself as he stepped outside. “Maybe we should wait till Sam gets back with the Impala,” he muttered.

Crowley glanced back at him, his black, wool coat dusted with white flecks of snow, though he seemed unaffected by the cold. “The station’s a block away. And didn’t you say that time was of the essence?”

“Yeah, but it’s snowing,” he complained, his voice sounding pathetic even to his own ears.

He stopped, turning to face him fully. “The great Dean Winchester - defeated by snow?”

“I just don’t see the point in walking in the cold when we can ride in a nice, warm car if we just wait a few minutes.”

“And yet when I suggested making good use of an empty motel room, you insisted that we needed to get to work.”

“Well, that…” Dean opened his mouth and then closed it again. “You know what, fine,” he snapped as he started walking forward again. “It’s not that cold, anyway. Let’s go.”

Just a couple seconds after he passed Crowley, a snowball hit him in the back of his neck, some of the snow slipping beneath his shirt. 

“Dammit, Crowley!” he shouted, spinning around just in time to get another snowball in the face.

“What’s wrong?” Crowley asked innocently, though his eyes were sparkling with laughter. “Didn’t you just say that it wasn’t very cold?”

Dean’s eyes narrowed. “You know what…” He bent down and started forming a snowball. As he threw it, though, Crowley disappeared, and then he felt yet another snowball hit him on the back of the head. “Oh, come on!”

“Too slow, darling.”

He turned and glared at him.

“Come on, give me your best shot!” Crowley challenged, arms open wide.

It took him a little while (and a lot more snowballs to the back), but he did eventually manage to hit Crowley in the face with a large snowball. A few minutes later, they were laughing and both of their coats were nearly white with snow from how many hits they had both taken. 

They didn’t even notice the Impala pulling up, until Sam had gotten out and was walking over to them. “What the hell, guys?” he demanded.

Crowley and Dean glanced at him, then made eye-contact with each other, a mischievous gleam in both of their eyes. Simultaneously, they both turned and threw the snowballs they had in hand at Sam, hitting him in the face and chest.

“Really?” he gasped, wiping the snow out of his eyes.

“What’s wrong, Sammy?” Dean taunted. “Afraid you can’t take us?”

Determination hardened Sam’s features, and then all three of them began rolling snowballs as quickly as possible.


	2. Thawing Out

**Summary for the Chapter:**

> Day 2: Keeping Warm by the Fire

[Originally posted by dean-winchester-crush](https://tmblr.co/ZOUoxk1_5GksS)

Dean was working just another hunt in the middle of winter - it wasn’t supposed to be anything more than a milk run, certainly not something that would lead to him trapped and freezing to death.

[Originally posted by imaginary-desires](https://tmblr.co/ZZJDLd2RRi4Fn)

Crowley got a call from Sam, worried because he couldn’t get a hold of Dean and asking him for his help finding him. 

[Originally posted by sooper-dee-dooper-natural](https://tmblr.co/ZWLrfi1_XLTqd)

It didn’t take him long to find Dean and teleport him back to his house.

[Originally posted by xmas-wonderland](https://tmblr.co/Z0I6yu2PG-6sc)

With a snap of his fingers, Crowley started a fire in the fireplace and moved the couch as close as possible. He sat Dean down on the couch and wrapped a blanket around his shoulders, but he was still shivering profusely.

[Originally posted by lucifersagents](https://tmblr.co/ZMY7jf2SQPfU2)

After regarding him for a few seconds, Crowley moved around the couch and sat down beside beside him, pulling him close. Dean didn’t say anything as he curled into his side - neither of them did. They sat in silence, staring into the fire, until Dean fell asleep. 

[Originally posted by tearinmyeye](https://tmblr.co/Zq5vod2Ma7s5p)

When Dean woke up the next morning, a silent agreement passed between the two of them, and they never discussed what had happened. But something had changed between them that night, and Dean wasn’t so sure it was a bad thing.


	3. A Winchester Family Christmas

**Summary for the Chapter:**

> Day 3: Spiked Eggnog
> 
> This is set in an AU post season 12, where Crowley somehow got brought back to life and Jack brought Mary back.

This was shaping up to be the best Christmas Dean had had in... ever. Jack had helped them get their mom back just a couple weeks ago, and now she seemed determined that all five of them (she, Sam, Dean, Castiel, and Jack, that was) have a proper, family Christmas. And without the day being tainted by some impending doom, Dean found that he was able to enjoy the holiday more than ever before.

He sipped on the eggnog that Sam had made (which seemed to be more whiskey than eggnog, not that he was complaining), and watched with a fond smile as Sam and Mary taught Jack some Christmas traditions. Castiel was pretending to help, but Dean knew that he was learning just as much as his adopted son.

For all the joy of the day, though, something just felt... off. It was like something was missing. At first, Dean wondered if it was his dad, but it wasn’t like he and Sam had ever had a proper Christmas celebration with him, and he had made his peace with his death a long time ago. So, maybe it was just all the losses that he had suffered in general - that would make sense, even if that answer still didn’t feel quite right to him.

Maybe it was the surreal feeling of a family Christmas, or maybe it was the eggnog, but suddenly, Dean found himself with his phone in hand, dialing a familiar number.

“Squirrel,” Crowley greeted him, his voice a touch more subdued than usual - Dean probably wouldn’t have noticed it if he didn’t know Crowley so well. “Don’t tell me you’re working on Christmas.”

“No, I’m... we’re having a real, old-fashioned family Christmas.” He gave a disbelieving laugh at being able to say those words. “With a little bit of Winchester dysfunction thrown in on top, of course.”

He chuckled. “Then, why are you calling me? Bored of the festivities already?”

“No.” He breathed in a deep breath. Even though he hadn’t really known what he was doing as he dialed the demon’s number, the pieces had since clicked into place. “What do you do to celebrate Christmas?”

“I don’t,” Crowley said, his voice clearly confused. “I’m a demon, and it’s not like I have any fond memories of the day from when I was human.”

“Well, maybe it’s time you make some.”

There was a pause. “What are you saying?” he asked slowly.

“Come over.” Dean wasn’t sure why his heart was pounding so loudly as he said the words, but it was getting harder to hear himself over it. “We have more than enough food.”

“What’s the matter? Don’t have enough dysfunction, so you need to add a demon into the mix?” He was trying to joke, but it sounded strained.

“No, I just...” He sighed. Time to bite the bullet. “I want you here. You’re part of this family.”

The pause was longer this time, and when Crowley spoke again, his voice seemed rougher than usual. “I’m pretty sure your mother and brother disagree.”

“They’ll come to terms with it. Eventually.”

“I don’t know, squirrel...”

“Did I mention we have some _really_ freakin’ strong eggnog?” he tried, determined not to give up.

He could almost hear Crowley’s smile break out across his face. “Whiskey or rum?”

“Whiskey, of course,” Dean scoffed in mock-offense. 

He knew full well that the next pause was just Crowley’s attempt to draw out the suspense. “Well, I do have a gift I need to get to you somehow.”

The smile that had been spreading over his face faltered. “I didn’t get you anything...”

“Yes, you did,” he interrupted, his voice firm. “I’ll see you soon.”


	4. Pretending

**Summary for the Chapter:**

> Day 4: Naughty or Nice
> 
> This is a sequel to the previous fic.

“Dean?” Sam asked, a frown in his voice. “What’re you doing?”

“Powering down the wards,” Dean muttered, bracing himself.

“What?” he snapped. “Why?”

“Because I invited Crowley.” He finished what he was doing and turned to see three pairs of wide eyes staring at him in disbelief (Jack was looking between Dean and the others in confusion).

“Why?” Sam asked again, slowly.

He sighed. “Because with everything he’s done for us… I think he deserves a good Christmas.”

“He’s a demon,” Mary protested.

“Yeah, and he died for us not too long ago. Look, the guy’s never had a good Christmas – he’s never had anyone to celebrate with. Now he does.”

“I think that sounds nice,” Jack spoke up.

Castiel looked down at him thoughtfully for a moment before he nodded at Dean. “Yes, I think it does.”

Sam glanced back and forth between Castiel and Dean, then he gave a resigned sigh. “Alright. Fine. Maybe you have a point.”

“Of course I do,” Dean said with a slight smirk before his gaze landed on his mom. “This isn’t gonna be an issue, is it?”

“No.” She shook her head. “If you trust him, then… I suppose he has done quite a bit in the way of proving himself.”

“Good.” He nodded, a relieved smile turning up the corners of his lips. “He should be here-”

“Now,” Crowley interrupted him as he appeared a little to his right.

Dean shot him an exasperated look. “Do you just wait in the shadows for me to say something like that, or what?”

“I just have excellent timing,” he insisted. “Merry Christmas, all.”

“Merry Christmas!” Jack immediately piped up.

“Merry Christmas, Crowley,” Castiel said politely, while Sam gave a little sigh, but still sounded sincere when he said, “Merry Christmas.”

Mary just nodded, but honestly, that was still progress.

“Yeah, merry Christmas,” Dean said softly as he stepped up to Crowley while Mary and Sam went to go check on the ham, and Castiel picked up some Christmas book to read with Jack. “Nice tie,” he added, reaching out to touch the red tie that Crowley had substituted his usual grey one for.

“Thank you,” he murmured, looking up into Dean’s eyes. “I save it for special occasions.”

He swallowed thickly as he nodded, belatedly realizing how intimate he had made this. Not only were they now standing mere inches from each other and staring into each other’s eyes, but Dean’s hand was resting on Crowley’s chest. He quickly dropped his hand as he looked away.

There had been… _something_ – between himself and Crowley for some time now, and after everything that had happened recently, he was more willing to admit it. But that didn’t mean he was ready to stop pretending it wasn’t there.

“So, have you been naughty or nice?” Crowley’s voice pulled him away from his jumbled thoughts.

He blinked at him. “What?”

He sighed. “Have you been naughty or nice?” he repeated slower.

Dean cleared his throat. That sounded a whole lot dirtier coming from Crowley than it did in a Christmas song. “Um… you tell me,” he muttered, struggling to gather his thoughts.

“Hmm… definitely naughty.” He winked. “Lucky for you, I like that.” He pulled a small gift box from behind his back and offered it out to Dean.

“Thanks, man,” he said as he took it. He pulled off the lid, and then his breath caught in his throat as he immediately recognized the small, polaroid picture inside. It was a picture of him and Sam, the day before he had left for college and Dean’s world had fallen apart – they had their arms around each other, and they were smiling, truly happy and unaware of what was to come. He remembered walking back into the hotel room that next day, after the fight that had ended with Sam leaving for what Dean had feared was for good, and seeing that picture on the nightstand. He had slipped it into his pocket and kept it on him, unbeknownst even to Sam, until the day that he had become a demon, and then, determined to distance himself from his brother, he had gotten rid of it.

Some part of Dean heard Sam calling for Castiel’s help with something, but he hardly noticed, entirely focused on the picture he had been sure he would never see again.

Eventually, he looked up at Crowley in disbelief. “How did you find this?” he breathed.

He shrugged, not quite looking at him. “It took a little bit of searching, but… it wasn’t too hard.”

“Thank you, I…” He swallowed thickly, unable to find the words to express what this meant to him. “Thanks.”

Crowley smiled as he looked up at him.

“Dean?” Dean had completely forgotten that there was anyone else in the room until Jack spoke up.

“Uh, yeah?” he muttered distractedly as he put the lid back on the box and turned to the nephilim.

“What was the tradition with mistletoe, again?” he asked curiously.

“Uh… you kiss whoever you’re standing under it with. Why?”

Jack looked up, and Dean followed his gaze, only just then noticing that he and Crowley were, in fact, standing under a clump of mistletoe. “So, you two have to kiss now?”

“Um… uh…” He struggled to come up with something to say, most of his focus on avoiding looking at Crowley.

“Well, we don’t _have_ to,” Crowley said, a smirk audible in his voice. “Dean could always step away.”

That was true, he could. He should. But… Before his brain was able to fully catch up to his actions, he grabbed Crowley by the tie and pulled him into a heated kiss.

“Dean?!” Sam’s aghast voice signaled his return to the room.

Dean pulled away, taking note of the thoroughly pleased expression on Crowley’s face, before turning to his brother, giving him a slightly sheepish grin.

“They were under the mistletoe,” Jack supplied.

“Still are,” Crowley pointed out, raising his hand to rest on Dean’s lower back.

A blush darkened Dean’s cheeks as he reached back to remove Crowley’s hand from his back, instead opting to intertwine their fingers together.

“You know what? I’m not even gonna touch this,” Sam muttered, shaking his head as he placed the ham he had been carrying down on the table. “Could you come help us carry the food out?”

“I did most of the cooking!” Dean protested.

“Yeah, but the sooner we get everything out here, the sooner we can eat.”

“Fine,” he sighed, reluctantly stepping out from under the mistletoe, though he didn’t drop Crowley’s hand. He was going to walk into the kitchen hand-in-hand with Crowley, and he didn’t care how his mom and Castiel would react. He was done pretending.


	5. Christmas Present

**Summary for the Chapter:**

> Day 5: Christmas Shopping

Dean had never realized how much he could hate Christmas shopping until his first Christmas dating Crowley. What the hell did you buy a _demon_ for Christmas? A filthy rich demon who could get anything he wanted with a snap of his fingers, at that. At the end of every day that he spent looking for the perfect present, he would get fed up and declare that he just wasn't going to get him anything, but then the next day, he'd be back to looking again.

It wouldn't be so bad, if it weren't for the fact that Crowley was the best gift-giver of all time, and he showered Dean with presents all year round. He couldn't even imagine what the guy would do for him for Christmas - certainly nothing that he could contend with. He was really starting to wish that Crowley was as selfish as he had once thought him to be. But no, it was as though his primary ambition these days was to spoil him.

It's on Christmas Eve that he comes to the conclusion that the best gift he can give him is his cooperation. So, he gives Crowley a week. One week to do whatever he wants, to take Dean wherever he desires, and he gives his word that he won't raise any objections.

The sparkle in Crowley's eyes when Dean tells him his present almost makes him regret it. Almost.


	6. Too Light

**Summary for the Chapter:**

> Day 6: Christmas Lights

In which Crowley takes Dean to a Christmas light show.

“You can’t actually be enjoying this.”

“Whyever not?”

“You’re a demon. Isn’t this a bit too… ‘light’ for you?”

“Ha ha. For your information, I happen to be enjoying this an exceptional amount.”

“Really?”

“You’re smiling more tonight than you generally do in a week, and as an added bonus, you’re pressing close to me to keep warm. So yes, I am very much enjoying myself.”


	7. White Christmas

**Summary for the Chapter:**

> Day 7: Christmas Trope - Fake Dating
> 
> This is an performers!AU based off the movie ‘White Christmas’. Sorry it seems a little rushed, I did as much as I could in the time I had.

Sam and Dean had always been inseparable. When they were kids, Sam would follow Dean around wherever he went, and unlike some big brothers, Dean didn’t mind one bit – he enjoyed it, even. It only made sense that when they grew up, they would end up working together. They were performers, spending their lives traveling from one city to another, up until they decided to buy their own theatre up by their Uncle Bobby’s inn. Their goal was to be able to recruit enough acts to have a variety show for the grand opening on Christmas Eve.

“A comedy act? Really?” Sam asked skeptically as he read over the bio for the act they were auditioning that night.

Dean shrugged as he rummaged through his closet. “They’re apparently pretty successful – consistently sold out shows in venues way bigger than ours.”

“So, why are they bothering to audition here if they’re doing so great?”

“Remember Gabriel?” he asked as he started to change his shirt. “One of the guys is his brother – he recommended us.”

Sam frowned. “Why would he do that?”

“I dunno,” he muttered, avoiding looking at his brother. “Guess he knew we were trying to open the place, and figured…”

“You asked him to, didn’t you?” he accused.

Dean sighed. “Okay, fine. I found out that Gabe’s brother was a successful comedian, so I thought I’d see-”

“Why, though? Comedians were never in our plan.”

“Yeah, but these guys will bring in a lot of business. We need that.” He cast Sam a sidelong glance. “And they’re pretty damn good looking, too.”

Sam gave an exasperated sigh. “Not this again. I’m not interested in dating anyone.”

“Well, you should be. You need to learn to relax, Sammy, you’re killing me over here.”

“I am perfectly relaxed,” he protested.

Dean scoffed. “No, you’re not. You don’t know how to stop working for five seconds!”

“Oh, and you do?” Sam demanded, crossing his arms over his chest. “I don’t see you dating anyone either, Dean.”

“Well, I’m a lone wolf. It’s different.”

He rolled his eyes. “Right. Well, I’ll start dating when you do.”

Dean sighed in temporary defeat. He’d bring it up again at some point, but he knew he wasn’t getting anywhere at the moment. Besides, it was about time for the audition.

Castiel and Crowley assumed the personas of an angel and a demon when they took the stage, and watching their banter, Dean could see why they were so successful. Even better, they were even more attractive in person, or at least Crowley was. Dean had a hard time taking his eyes off of him.

“Gotta admit he’s hot, Sammy,” Dean leaned in to mutter quietly.

“Uh… yeah,” Sam surprisingly breathed in reply. That was enough to tear Dean’s eyes away from the stage for a few seconds – long enough to see that Sam’s eyes were fixed on Castiel, the corners of his lips curling up as the comedian spoke. Well, this was promising.

After Castiel and Crowley finished their skit, Sam and Dean invited them to sit and talk with them to get to know them a little more. As Dean saw how little their demeanor changed as they walked off the stage, he had to wonder just how different their comedy personas were from themselves.

“Thank you for coming out to audition,” Dean said as Castiel took the seat across from him, and Crowley sat beside him.

“Honestly, I do not believe we would have if Gabriel had not recommended it,” Castiel admitted.

“Yeah, about that-” Sam started, but Dean hastened to cut him off.

“That was really nice of him to do. So, how did you two get your start?”

“We were at a comedy club when there was an earthquake,” Castiel explained. “The building collapsed, and I would have been crushed, had it not been for Crowley.”

Dean looked at Crowley with wide eyes. “Seriously?”

“It was no big deal,” Crowley said with a shrug. “I only broke my arm saving him.”

Castiel shot him a poorly disguised glare. “As a way of repaying him, I agreed to partner with him.”

“And it was the best decision of your life.”

“It was… certainly profitable.”

“Well, I think we’d love to have you on here,” Dean said, looking at his brother. “Don’t you think, Sammy?”

“Yeah, definitely,” Sam agreed.

“Of course you would,” Crowley dismissed their words with a wave of his hand. “But we’re not sure we’re interested.”

Dean forced his expression to remain calm. “Oh?”

“You’re wanting to open with a big Christmas Eve show, correct? Have you checked for the projected forecast?”

“No snow,” Sam nodded. “We understand how-”

“No one comes to this area unless it’s to ski,” Crowley interrupted. “And they won’t be doing that if there’s no snow, now will they? Therefore, this lovely little theatre will not take off. We’re not signing onto something doomed to fail.”

“Yeah, but if we get the word out that the two of you will be performing a never-before-seen act, that’ll get people in, snow or not,” Dean pointed out.

“Oh, so now you want us to write up a whole new skit, just for you?”

“We have been working on something,” Castiel reminded his partner. “We could do it.”

“Look, we’re not trying to put you out,” Sam said with a small sigh. “We get that this place might be a little small-scale for you, but… I really enjoyed your act and would be honored to have you as a part of our show.”

He smiled at him. “Perhaps it would be beneficial for us to get an idea of what the rest of the show is like – that way we can make an informed decision. Could we see what you do?”

“You want us to perform for you?” He looked at his brother questioningly.

Dean shrugged. “Seems fair enough. Just keep in mind that we haven’t warmed up our voices.”

He and Sam got up onto the stage, deciding with little discussion to do one of their oldest songs. It wasn’t a fancy performance, by any means – it was mostly just them singing, though there were some simple steps involved – but it had been perfected over the years. When they were finished, they walked back down from the stage, about to resume their seats.

Crowley stood before either of them could sit down. “Dean. What area of the business are you in charge of, exactly?”

“Uh, I write the songs and do the marketing,” Dean answered cautiously.

“Excellent. Marketing is just what I wanted to discuss. Could we step away for a moment?”

He frowned slightly, unsure of what exactly Crowley’s motivation was. But stepping away with him would leave Sam and Castiel on their own…. “Sure.”

“Are you sure you don’t want me to-?” Castiel started, but Crowley cut him off.

“No, best to simplify the conversation. You stay here – get to know Sam.”

Dean didn’t miss the way Castiel’s eyes narrowed as Crowley turned away, but he didn’t pause to think much of it before following him backstage.

“Your brother single?” Crowley asked, peering out from the curtains at the couple sitting at the table.

“Irritatingly so,” he sighed, the pieces starting to click into place. “He refuses to relax.”

“He can’t be as bad as Castiel,” he said as he turned to face him. “He’s stiffer than the angel he pretends to be on stage. His inability to do anything other than work is starting to ruin my life.”

Dean started to smile. “You thinking what I’m thinking?”

“I’m thinking that it will be a pleasure doing business with you, Mr. Winchester.” He extended his hand to him and Dean shook it.

“Likewise.”

* * *

Dean and Crowley had their work cut out for them. Sam’s eyes consistently drifted towards Castiel whenever he entered the room, but whenever Dean tried to push him in his direction… nothing. And he couldn’t get a read on Castiel to save his life.

“You’re sure he’s interested?” he asked Crowley a few days after they had hired them on, as they had lunch at Bobby’s inn. It was where Sam and Dean were living currently, and they had gotten Crowley and Castiel rooms there for a discounted rate.

“Definitely,” Crowley said confidently. “He can’t take his eyes off Sam whenever you two are performing.”

“Yeah, Sam’s the same way with him,” Dean sighed. “I just can’t get him to do anything about it.”

“Well, Castiel is definitely _not_ going to make the first move.”

“So, I guess we’ll just have to make it for them.”

Crowley looked at him thoughtfully. “What do you suggest?”

He thought about it for a minute. “Sammy likes to go on runs at an ungodly hour in the morning – always ends with him relaxing in the dining room before anyone else is up. Think you can get Cas there?”

“I’ll see what I can do.”

* * *

The next morning, the two of them watched victoriously from outside the window as Sam and Castiel talked, and then Sam leaned in for a kiss. Satisfied that Castiel was responding well to his advances, Dean and Crowley slipped away to Crowley’s room to share a celebratory drink.

When Dean met up with his brother later that day, though; he didn’t look anywhere close to happy.

“Hey, Sammy,” Dean greeted him tentatively. “What’s up?”

“Nothing,” Sam sighed. “Just… rough morning.”

He frowned. “Rough…?” He had made out with Castiel that morning! How was that rough? “What-?” Before he could even figure out what to ask, though; Castiel entered the room.

“Hi, Sam,” he said, his face lighting up when he spotted him.

The color drained from Sam’s face. “Oh, uh… hi,” he muttered without looking at Castiel. “I should… go.” Before either of them could say another word, he all but ran out the door.

Dean looked at Castiel, searching for some kind of explanation, but he was just frowning at the spot where Sam had previously been standing, his forehead creased in confusion.

“Is something wrong?” he asked worriedly, turning to look at Dean.

 _Great question._ “Uh… no, no, I’m sure everything’s fine. Don’t worry about it, Cas.” He quickly excused himself from the room, then pulled out his phone and sent Crowley a quick text, _‘Drinks tonight?’_

* * *

By the time Dean got to the bar, Crowley was already there and had ordered Dean his usual.

“Thanks,” he said as he sat down, downing half of his whiskey in one drink.

“Sam as moody today as Cassie was?” Crowley guessed.

“Yeah,” Dean sighed. “I dunno what the deal is! They seemed happy this morning, but then Sam just…” He shook his head, taking another drink.

“Yes, Castiel looked like a dejected puppy when he showed up for rehearsal today. One of the many reasons I fail to see the point in relationships.”

“Tell me about it,” he muttered.

Crowley arched an eyebrow at him. “Do you think that might be Sam’s problem?”

Dean didn’t even have to think about the question before shaking his head. “No way. Sam’s not like me. Sure, he’s been refusing to find himself someone special, but I can tell he still wants that. He’s one of those people who looks wistfully at old married couples.”

“Castiel, too.” He shook his head slightly. “So, what could be holding Sam back, then?”

Dean thought about it as Crowley waved for the bartender to get them another round of drinks. “Maybe…” he murmured softly.

“What?” Crowley asked eagerly.

“His last relationship, it… well, it wasn’t a good one,” Dean explained hesitantly, knowing that Sam wouldn’t be comfortable with him sharing too many details with Crowley. “It drove a wedge between us. Some of the things he says sometimes… maybe he’s worried that that might happen again. We’ve always been so close, it… well, it was a hard time.”

“So, what do we do?”

“I don’t know,” he sighed. “I talk to him about it, I guess. Not sure how much good it’ll do, though.”

“Well, it’s a start. Until then…” He raised his glass. “We drink.”

It was a couple drinks later that an idea started to form at the edge of Dean’s mind. _“I’ll start dating when you do,”_ Sam’s words echoed in his mind.

“I’ve got it!” he suddenly exclaimed, slamming down his empty glass.

Crowley looked at him in surprise. “You’ve got… what, exactly?”

“How to get Sam to date Cas! I need a boyfriend – or a girlfriend, doesn’t really matter.” He smiled at Crowley triumphantly, while the other man looked at him as though concerned that he might have had a few too many drinks.

“I thought you said you didn’t do relationships?” he asked slowly.

“I don’t. But if I’m in a relationship, he’ll see that it’s okay for him to be in one.”

“Alright… that’s not an _altogether_ stupid idea. But just who do you plan on jumping into a relationship with up here, in the middle of nowhere?”

“I dunno,” Dean muttered, his smile dropping as he looked down at the new glass that had been placed in front of him. “I mean… it would probably help to be someone I know…”

“I may not be an expert in relationships, but I do believe that’s rather important.”

“And preferably someone I’m attracted to,” he continued thoughtfully. “And – and click with. Someone who’s smart, and… makes me laugh.”

“Yes, and how exactly do you plan to find Mr. or Miss Perfect?” Crowley asked reasonably.

“I don’t…” He froze before slowly turning back to Crowley. “I think I already have.”

“What do you…?” His expression dropped. “You cannot be serious.”

“Well, why not?” Dean asked. “You’re single, we – we get on well, don’t we?”

“Yes, but-”

“And you… I mean, you do find me at least somewhat attractive right?” he asked uncertainly. Sure, Crowley flirted with him occasionally, but that didn’t necessarily mean that he was attracted to him. Crowley just had that kind of personality.

He rolled his eyes. “There isn’t a soul alive that _wouldn’t_ find you attractive, Dean.”

Dean smiled down at his drink, his cheeks heating up slightly.

“But I don’t date,” Crowley continued.

“Not even to get Cas off your back?” he pressed, looking back up at him.

He scowled. “How long?” he asked after a few seconds.

“I dunno… a couple weeks?”

He sighed as he took a sip of his drink. “Fine.”

“Really?” Dean asked hopefully.

“I want those two morons to get together, so I’ll do what it takes.” He set his glass down and turned to face him. “Now, let’s make it official.”

“What…?”

Crowley grabbed him by the collar and pulled him into a kiss.

* * *

“You know,” Dean said as he got dressed the next morning. “I’m kinda liking this plan.”

Crowley chuckled from where he still lay on his bed. “It does have its moments, doesn’t it? I would have gotten you into bed sooner, but I have a policy against sleeping with coworkers.”

He raised his eyebrows at him. “Hey now, you don’t _know_ you would have gotten me into bed. You would have _tried.”_

“Oh, please.” He rolled his eyes as he got up and rested his hands on Dean’s hips. “You would’ve been putty in my hands.”

“I really wouldn’t have been.”

“No?” He leaned in, catching Dean’s ear between his teeth. “Too bad you have to be going,” he murmured in a low voice. “Otherwise I would bend you over the bed right now.”

He tried and failed to suppress his shiver.

Crowley smirked as he stepped back. “Like I said – putty.” With that he turned away and started getting dressed.

Dean sighed as he continued getting ready, realizing that he wasn’t going to win this. Maybe he had gotten in over his head with Crowley. But he had to admit, if he _were_ to actually date someone – not that he ever would – Crowley was just about the only person he could imagine he would. He certainly wasn’t going to consider dating him for real, though. No, as soon as Sam and Castiel were together, they could go back to being friends. Though… maybe they could still sleep together, on occasion.

He wasn’t sure how he managed to get so lucky, but as he walked out the door, Sam was coming down the hall.

His brother stopped when he saw him. “Dean?” His eyes narrowed. “This is Crowley’s room.”

“Uh, yeah,” Dean said innocently. “Yeah, it is.”

He sighed. “Seriously? Didn’t we decide that sleeping with coworkers is unprofessional?”

“No. We decided that _one-night stands_ with coworkers are unprofessional.”

Sam’s eyebrows furrowed in confusion. “If this isn’t a one-night stand, what is it?”

On cue, the door opened and Crowley stepped out, his arm sliding naturally around Dean’s waist. “Oh, morning, moose.” He looked up at Dean. “Lunch around noon?”

“Sounds great,” Dean said with a smile.                                                           

He pecked him on the lips, then turned and walked off.

Dean turned back to Sam, who was blinking at him in disbelief. “You and Crowley? For real?”

“Yeah.” He shrugged. “Why not?”

“I mean, he doesn’t exactly come across as… cuddly.”

“He was plenty cuddly last night.” That part was actually true, too. The last thing that Dean had expected was for Crowley to want to cuddle after sex, but he had been pretty insistent about it – not that Dean had been putting up much of a fight.

“What happened to you being a lone wolf?” Sam asked.

“I don’t know,” he sighed. “Crowley just… he makes me happy.”

His expression softened into a smile. “Well, if he makes you happy, that’s good enough for me.”

“Thanks, Sammy.” They fell into step beside each other as they made their way down to the dining room. “You know, you could be happy, too.”

“I am happy,” Sam insisted, but his smile slipped slightly as he spoke, making the words that much less convincing.

* * *

If Dean and Crowley had thought that Sam and Castiel would be ready to jump in together the moment Dean was off the market, they were sorely mistaken. Two weeks later, and not only were they still not together, but Sam was still doing everything in his power to avoid him.

“I don’t get it!” Dean exclaimed as he and Crowley sat in what might as well be referred to as their room these days. _“Nothing_ has changed…. Did we get it all wrong?”

“We can’t have.” Crowley shook his head. “We saw them make out, Cassie is still pining over Samantha… how’s he doing?”

“He seems sadder every day,” he sighed, looking at the ground. “I’m starting to wonder… maybe us dating is doing more harm than good.”

He was silent for several seconds, then Dean heard the rustle of his clothing as he stood. “Take off your shirt.”

He looked up at him in disbelief. “Crowley, sex is _not_ going to help with-”

“Take off your shirt,” he repeated firmly.

Dean sighed and stood up, stripping his shirt over his head and throwing it down onto the chair.

“Lay down on your stomach,” Crowley instructed, motioning towards the bed.

He shot him a skeptical look, but did as he was told. A few seconds later, the bed dipped as Crowley sat behind him, and then he began rubbing his shoulders.

Dean sighed. “That feels good.”

Crowley hummed in acknowledgement of his words, but otherwise remained silent as he massaged Dean’s back and shoulders.

“I lied,” Dean admitted quietly a few minutes later. “About why I want Sam in a relationship so bad.”

He was easily able to translate Crowley’s continued silence – it was an invitation to continue, without making him feel any pressure to do so. It was funny, how well he understood Crowley, after knowing him for just a few weeks.

“I mean, I guess – yeah, I do want him to relax, but… that’s not why. I just…” He took a deep breath, feeling, not for the first time, as though he were being crushed under the weight of his guilt. “I’ve looked out for him my entire life, and I don’t resent that, but… I wish he had someone else who could be there for him for once…. I wish that I could have at least some semblance of my own life that’s not completely centered around taking care of Sammy….” He shook his head, the tears sparkling in his eyes mercifully not visible to Crowley. “I’m selfish.”

“Dean.” Crowley’s voice was soft, yet firm. “You are the most unselfish person I know.”

“But I’m not,” he protested.

“It was your idea to buy a theatre in this area, was it not?”

“Yeah…” Dean answered, confused as to where he was going with this.

“There are many locations throughout the country that would have been far more profitable for you and your brother, particularly with how this winter is predicted to go. Of course, one bad winter could put your uncle out of business…. If only there were something more than ski slopes to draw people in, like a theatre that features a few well-known talents. Am I wrong about your reasoning?”

“No,” he admitted with a sigh.

“At first, I thought you were an idiot,” Crowley continued. “The worst businessman in show business that I had seen. And then I thought you were just a hopeless sap, and… well, I do still think that, but I’m starting to see that that might not be such a bad thing.”

That managed to get a laugh out of him. “Gee, thanks.”

“My point is, you are the most compassionate person I have ever met. It’s not selfish for you to want your own life – it’s normal.”

Dean was quiet as that sunk in. “Thanks,” he muttered softly as he sat up, shifting to face Crowley and brushing their lips together lightly. “Even if you are right, though; that doesn’t mean I should be interfering with my brother’s life. Maybe we should… call it quits.” He swallowed down the lump in his throat, surprised by just how difficult that had been to say. It wasn’t like he was actually breaking up with Crowley – they had never really been together in the first place. But… maybe some foolish part of Dean was starting to wish that there had been more to their little charade. He knew better than to hope that Crowley felt the same, though. A real relationship with him was never going to happen.

Crowley was silent for a few seconds as he stared down at his lap, but then he nodded. “Yes, you’re… probably right.”

* * *

“I’m sorry, Sammy,” Dean finished his confession. “We shouldn’t have tried interfering in your lives like that.”

Sam shook his head, clearly a bit overwhelmed by what Dean had just dumped on him. “I just… I don’t get it. Why did you think dating Crowley would make Cas and I get together?”

“Well, you… after how Ruby came between us, I thought that maybe you were worried that might happen again.”

“No, that’s… that’s not it at all,” he sighed.

Dean frowned. “So, what is it, then? Because I know you like him, Sammy. What’s holding you back?”

He sighed again. “It’s… my past. Cas is an amazing person, and he has no idea the things I’ve done… Ruby, the drugs… if he knew about all of that, he wouldn’t want anything to do with me. And I’d rather not have to hear him say it.”

“That is not true,” a voice spoke from the doorway.

Sam and Dean spun around to see Castiel standing there, Crowley right behind him.

“Cas, I…” Sam started, but Castiel interrupted.

“Sam, if it is all the same to you, I would like to opportunity to make the decision of whether or not I want anything to do with you myself. And as it happens, I want a lot to do with you – regardless of your past.”

Dean grinned as he slipped out of the room, deciding to leave the two of them to talk things out.

“So, you led him here?” he asked as he closed the door behind him.

“Of course,” Crowley answered proudly.

He chuckled as they set off down the hall together. “What happened to us not interfering anymore?”

“That wasn’t interfering, that was merely giving Castiel all the information. It’s amazing how admitting one little thing can change so much.”

Yeah. Like, how if Dean were to admit that he had somehow managed to actually fall for Crowley, his ex-fake-boyfriend would never want to talk to him again.

* * *

With Christmas Eve came a sold out show and high spirits for most of the crew. Dean was pretty sure he was the only one who’s mood was less than one hundred percent, but he was happy for his brother and for the business they were bringing Bobby, even if his own life had taken an unpleasant turn.

And really, it was a ridiculous. A month ago, he had hated the idea of being in a relationship. But a month ago, he hadn’t known Crowley… possibly the only person in the world who hated relationships more than he did. Just his luck.

“You know,” Sam said as he stepped up beside him. “Just because it was fake, doesn’t mean it couldn’t be real.”

Dean tore his gaze from the door that Crowley had just left through to stare at his brother. “I don’t know what you’re talking about,” he denied.

He arched an eyebrow at him skeptically. “Right…. Look, you and Crowley were good together – real or not. So, if you like him…”

“I don’t,” he lied, turning to straighten the already straight stack of programs. “He’s just a friend.”

“You don’t stare at your friends like that. Dean, weren’t you just getting onto me a few days ago for denying myself with Cas? Now here you are, doing the same thing.”

“No, I’m not, Sam,” he snapped, looking up at him again. “Because Cas actually liked you back.”

Silence fell between them, and Dean cursed himself for saying that aloud as he turned back to the programs.

“Did Crowley tell you that?” Sam asked softly.

“He might as well have,” he muttered bitterly.

Sam started to say something else, but Dean rounded on him. “Just drop it, Sammy.”

“Okay…. I’m sorry.”

He sighed. “It’s fine, just… don’t say anything to him, okay?”

He hesitated before he reluctantly agreed. “But maybe…”

“Whatever you’re going to say, the answer is no. Now, we open in five hours. We have work to do.”

* * *

It was an hour till curtain when Castiel came rushing in. “Dean! You need to look outside.”

Dean frowned. “Why?” What was going wrong now?

“Just trust me,” he insisted with a smile.

He looked at him curiously before shaking his head resignedly, and then walking out the back door. Immediately, the vision was obscured by white flurries as snow fell all around him. A joyful laugh escaped him as he walked out further, reaching out a hand and watching the snow flakes land on it, then instantly melt.

“A white Christmas, after all,” Crowley’s voice rang out as he stepped up beside Dean.

Dean smiled at him. “Looks like you were wrong.”

“Hmm… perhaps it wasn’t the only thing I was wrong about,” he murmured, looking ahead.

He frowned. “What do you mean?”

“Dating. It isn’t so bad, really. At least… dating you isn’t.” He looked up at him, and Dean’s breath caught in his throat.

“What are you saying?” he asked, afraid to hope.

“I’m saying – let’s date for real this time.”

A smile spread across Dean’s face, but before he acted on the impulse to grab Crowley and pull him into a kiss, he paused. “Wait. That wasn’t a question.”

“No,” Crowley said matter-of-factly.

“Well… how do you know I want to date you?”

He rolled his eyes, then glanced behind them. Dean followed his gaze to see Sam and Castiel in the doorway, pretending not to be watching them.

“Are you…?” Dean shook his head as he turned back to Crowley. “Sam told me he wouldn’t tell you!”

“Oh, he didn’t. He told Castiel-”

“Who told you,” he sighed. “Guess I can’t complain.”

“We did have it coming,” Crowley pointed out. “I have to admit, I’m not entirely sure whether your brother was acting in revenge, or in reciprocation.”

“Prob’ly both.” Dean shrugged as he turned back towards the door. “Well, I suppose we should get back to work. We do have a show to put on.”

“One thing first.” He grabbed Dean’s hand, spinning him back around and pulling him into a kiss. “Okay,” he said as he pulled away. “Now we can get to work.”

* * *

The show was a great success. Nothing went disastrously wrong, and the audience seemed to enjoy it. The final act was Crowley and Castiel, and Sam and Dean watched them from the wings, with rather similar smiles on their faces.

“Now,” Crowley said as they concluded their act. “Let’s hear it one more time for the very talented, and incredibly handsome men who made tonight possible – Sam and Dean Winchester. Sorry, ladies and gents, but they’re both spoken for.”

Dean rolled his eyes as he and Sam took the stage again for the finale of ‘White Christmas’. The rest of the cast gradually came out and joined them, some in song and some in dance; though, Crowley and Castiel remained on the sidelines, whispering together in a way that made Dean immediately suspicious.

He didn’t have to wait long to learn just what they were whispering about. As the song came to an end, and all of the cast lined up to take a bow – Castiel and Crowley on either side of Sam and Dean – the brothers had barely finished singing before they were both seized and pulled into a kiss. There were definitely some gasps, laughs, and cheers from the audience, but Dean didn’t pay them any mind, his entire focus on Crowley’s lips. The two of them didn’t break apart until the curtain had been drawn shut, separating them from the audience.

“I hope you have a very merry Christmas, Dean,” Crowley said as he drew back to look Dean in the eyes, his expression far softer than it usually was.

Dean was probably grinning like an idiot, but he couldn’t bring himself to care, at the moment. “I think it’s gonna be the best one yet.”

**Notes for the Chapter:**

> I hope you enjoyed these! Merry Christmas!


End file.
